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• W4381943670 endingPage "1281" @default.
• W4381943670 startingPage "1271" @default.
• W4381943670 abstract "The binucleophilic properties of 1,2-aminothiol and its rare occurrence in nature make it a useful reporter for tracking molecules in living systems. The 1,2-aminothiol moiety is present in cysteine, which is a substrate for a biocompatible click reaction with heteroaromatic nitriles. Despite the wide range of applications for this reaction, the scope of nitrile substrates has been explored only to a limited extent. In this study, we expand the chemical space of heteroaromatic nitriles for bioconjugation under physiologically relevant conditions. We systematically assembled a library of 116 2-cyanobenzimidazoles, 1-methyl-2-cyanobenzimidazoles, 2-cyanobenzothiazoles, and 2-cyanobenzoxazoles containing electron-donating and electron-withdrawing substituents at all positions of the benzene ring. The compounds were evaluated for their stability, reactivity, and selectivity toward the N-terminal cysteine of model oligopeptides. In comparison to the benchmark 6-hydroxy-2-cyanobenzothiazole or 6-amino-2-cyanobenzothiazole, we provide highly selective and moderately reactive nitriles as well as highly reactive yet less selective analogs with a variety of enabling attachment chemistries to aid future applications in bioconjugation, chemical biology, and nanomaterial science." @default.
• W4381943670 created "2023-06-26" @default.
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• W4381943670 date "2023-06-24" @default.
• W4381943670 modified "2023-10-14" @default.
• W4381943670 title "Tunable Heteroaromatic Nitriles for Selective Bioorthogonal Click Reaction with Cysteine" @default.
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• W4381943670 doi "https://doi.org/10.1021/acs.bioconjchem.3c00163" @default.
• W4381943670 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/37354098" @default.
• W4381943670 hasPublicationYear "2023" @default.
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